2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 'OH 1) NaCN 2) H* 1) NaBH4 2) H3O+ OH Group -H A Value (kcal/mol) Defined as 0.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter14: Elimination
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Problem 46CTQ
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2. Our knowledge of chair conformations allows us to use them to determine a great deal about
a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single
conformation can help us learn about the spatial requirements and energetics of a reaction.
Consider the following two reaction products:
CN
1) NaCN
2) H+
OH
1) NaBH4
2) H3O+
OH
Group
-H
-CN
A Value (kcal/mol)
Defined as 0
0.2 kcal/mol
-OH
1.0 kcal/mol
c. For any products that do have the most stable conformation, does our understanding of
the mechanism allow for ‘thermodynamic control'?
d. If one of the products is not the most stable, can you explain the observed product based
on ‘kinetic control'? (Does the most easily formed transition state result in the observed
product?) Consider the chair-like conformation of the starting material.
Transcribed Image Text:2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.
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